A novel scission of alkyl-carbonyl C-C bond by alkyl p-hydroxyphenyl ketones

Methyl, ethyl, n-propyl, and benzyl p-hydroxyphenyl ketones and 6-hydroxy-1 -tetralone are shown under the condition of ethylene ketal formation to und ergo alkyl-carbonyl C-C bond scission, but not with p-hydroxy-benzophenone, p-hydroxyisobutyrophenone, and 5-hydroxy-1-indanone. It is suggested that the scission is preceded by an aldol condensation, followed by a phenolic h ydroxyl participation with scission of the C-C in the beta -hydroxy-ketone formed. It should be noted that the participation by phenolic hydroxyl is a lso the cause of nonformation of ethylene ketals by those ketones mentioned .